Filipin

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Filipin

Filipin is a mixture of four different fluorescent molecules from the group of polyene - macrolides , which can bind to cholesterol and have a fungicidal effect.

properties

Filipin was first isolated in 1955 by chemists at Upjohn from the mycelium and cell culture supernatants of Streptomyces filipinensis . The actinomycete Streptomyces filipinensis came from a Philippine soil sample, from which the name is derived. The Filipin complex is a mixture of at least four molecules: Filipin I (4%), II (25%), III (53%) and IV (18%).

The fungicidal effect of Filipin presumably results from a destabilization of the cell membrane and consequently a perforation of the cell. Due to the binding of cholesterol, and the fluorescence Filipin is in biochemistry as a fluorescent dye for staining lipid rafts used for the diagnosis of type C of Niemann-Pick disease , and in concentrations of from about 3 ug / mL is it to inhibit the endocytosis via Used caveolae .

Web links

Individual evidence

  1. ^ GB Whitfield, Thomas D. Brock , A. Ammann, D. Gottlieb, HE Carter: Filipin, an Antifungal Antibiotic: Isolation and Properties . In: J. Am. Chem. Soc. . 77, No. 18, 1955, pp. 4799-4801. doi : 10.1021 / ja01623a032 .
  2. ↑ Ceder, O .; Ryhage, R .: The Structure of Filipin . In: Acta Chem. Scand. . 18, 1964, pp. 558-561. doi : 10.3891 / acta.chem.scand.18-0558 .
  3. ↑ Bergy, ME; Eble, TE: Filipin Complex . In: Biochem. . 7, No. 2, 1968, pp. 653-659. doi : 10.1021 / bi00842a021 .
  4. ↑ MR Van Leeuwen, EA Golovina, J. Dijksterhuis: The polyene antimycotics nystatin and filipin disrupt the plasma membrane, whereas natamycin inhibits endocytosis in germinating conidia of Penicillium discolor. In: Journal of Applied Microbiology . Volume 106, Number 6, June 2009, pp. 1908-1918. doi : 10.1111 / j.1365-2672.2009.04165.x . PMID 19228256 .
  5. ↑ G. Gimpl, K. Gehrig-Burger: Cholesterol reporter molecules. In: Bioscience Reports . Volume 27, Number 6, December 2007, pp. 335-358. doi : 10.1007 / s10540-007-9060-1 . PMID 17668316 .
  6. ^ MT Vanier: Niemann-Pick disease type C. In: Orphanet Journal of Rare Diseases . Volume 5, 2010, p. 16. doi : 10.1186 / 1750-1172-5-16 . PMID 20525256 . PMC 2902432 (free full text).
  7. ↑ PA Orlandi, PH Fishman: Filipin-dependent inhibition of cholera toxin: evidence for toxin internalization and activation through caveolae-like domains. In: Journal of Cell Biology . Volume 141, Number 4, May 1998, pp. 905-915. PMID 9585410 . PMC 2132770 (free full text).